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Yuste F, Linares AH, Mastranzo VM, et al. Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides. J Org Chem. 2011;76(11):4635-44doi: 10.1021/jo2006335.
Yuste, F., Linares, A. H., Mastranzo, V. M., Ortiz, B., Sánchez-Obregón, R., Fraile, A., & Ruano, J. L. (2011). Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides. The Journal of organic chemistry, 76(11), 4635-44. https://doi.org/10.1021/jo2006335
Yuste, Francisco, et al. "Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides." The Journal of organic chemistry vol. 76,11 (2011): 4635-44. doi: https://doi.org/10.1021/jo2006335
Yuste F, Linares AH, Mastranzo VM, Ortiz B, Sánchez-Obregón R, Fraile A, Ruano JL. Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides. J Org Chem. 2011 Jun 03;76(11):4635-44. doi: 10.1021/jo2006335. Epub 2011 May 03. PMID: 21506555.
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J Org Chem. 2011 Jun 03;76(11):4635-44. doi: 10.1021/jo2006335. Epub 2011 May 03.

Methyl sulfinates as electrophiles in Friedel-Crafts reactions. Synthesis of aryl sulfoxides.

The Journal of organic chemistry

Francisco Yuste, Angélica Hernández Linares, Virginia M Mastranzo, Benjamín Ortiz, Rubén Sánchez-Obregón, Alberto Fraile, José Luis García Ruano

Affiliations

  1. Instituto de Química, Universidad Nacional Autónoma de México, Coyoacán, México D F. [email protected]

PMID: 21506555 DOI: 10.1021/jo2006335

Abstract

The Friedel-Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR(2)), provides alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.

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